CN1974674A - Colorant compounds - Google Patents

Colorant compounds Download PDF

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CN1974674A
CN1974674A CNA2006101631815A CN200610163181A CN1974674A CN 1974674 A CN1974674 A CN 1974674A CN A2006101631815 A CNA2006101631815 A CN A2006101631815A CN 200610163181 A CN200610163181 A CN 200610163181A CN 1974674 A CN1974674 A CN 1974674A
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alkyl
scheme
alkaryl
heteroatoms
ring
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CN1974674B (en
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J·H·班宁
B·吴
C·W·贾格
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Xerox Corp
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Xerox Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/20—Monoazo compounds containing cobalt
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/34—Hot-melt inks

Abstract

Disclosed are colorant compounds of the formulae and wherein R 1 , R 2 , R 3 , M, A, E, G, J, m, n, and p are as defined herein.

Description

Colorant compound
Technical field
Colorant compound is disclosed at this.More specifically, at this colorant compound that is specially adapted to hot melt or phase change ink is disclosed.
Background technology
Although known composition and method are suitable for their desired purpose, but need be specially adapted to the colorant compound of phase change ink, the colorant compound that need have required degree of heat stability, the colorant compound that need show required solubleness degree at the carrier that is used for phase change ink, need with the compatible colorant compound of phase change ink carrier of the energy requirement operation that can adopt reduction, the colorant compound that need in phase change ink, show required high chroma, the colorant compound that need in phase change ink, show satisfactory tone, the colorant compound that need in phase change ink, show high light-fast fastness degree, need when being incorporated into phase change ink in the colorant compound that shows the diffusion of relative low degree when printing and penetrate into different colours in abutting connection with printing zone, need to handle the safe colorant compound and need be able to produce colorant compound with the print that reduces stack height.
Summary of the invention
The colorant compound of following formula is disclosed at this:
Figure A20061016318100081
With
Figure A20061016318100091
R wherein 1, R 2And R 3Each is hydrogen atom independently of one another, alkyl, comprise linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and unsubstituted alkyl, and wherein heteroatoms can or can in alkyl, not exist, aralkyl, comprise and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and wherein heteroatoms can or can be not in the aryl of aralkyl or moieties, do not exist, or alkaryl, comprise and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, with replacement or unsubstituted, and wherein heteroatoms can or can be not in the aryl of alkaryl or moieties, do not exist, condition is at R 1+ R 2+ R 3In, get rid of the atom in any substituting group, carbon atom and heteroatomic overall number are at least about 18, M is an atoms metal, each A, each E and each G represent the substituting group on phenyl or the pyrazolone ring independently of one another, wherein G also can be a hydrogen atom, m is an integer 0,1 or 2, p is an integer 0,1,2,3 or 4, J represents (i) hydrogen atom, (ii) alkyl (comprises linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and substituted alkyl not, and wherein heteroatoms can or can in alkyl, not exist), (iii) aryl (comprises and replacing and unsubstituting aromatic yl, and wherein heteroatoms can or can in aryl, not exist), (iv) aralkyl (comprises and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, and ring-type or acyclic, and wherein heteroatoms can or can be not in the aryl of aralkyl or moieties, do not exist), or (v) alkaryl (comprises and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, and ring-type or acyclic, and wherein heteroatoms can or can be not in the aryl of alkaryl or moieties, do not exist), wherein the two or more substituting groups on phenyl or the pyrazolone ring can be combined together to form ring and n represents integer 1,2 or 3.
Embodiment
Following embodiment is disclosed at this.
The colorant compound of scheme 1. following formulas:
With
Figure A20061016318100102
R wherein 1, R 2And R 3Each is hydrogen atom independently of one another, alkyl, comprise linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and substituted alkyl not, and wherein heteroatoms can or can in alkyl, not exist, aralkyl, comprise and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and wherein heteroatoms can or can be not in the aryl of aralkyl or moieties, do not exist, or alkaryl, comprise and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and wherein heteroatoms can or can be not in the aryl of alkaryl or moieties, do not exist, condition is R 1+ R 2+ R 3The middle atom of getting rid of in any substituting group, carbon atom and heteroatomic overall number are at least about 18, M is an atoms metal, each A, each E and each G represent the substituting group on phenyl or the pyrazolone ring independently of one another, wherein G also can be a hydrogen atom, m is an integer 0,1 or 2, p is an integer 0,1,2,3 or 4, J represents (i) hydrogen atom, (ii) alkyl (comprises linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and substituted alkyl not, and wherein heteroatoms can or can in alkyl, not exist), (iii) aryl (comprises and replacing and unsubstituting aromatic yl, and wherein heteroatoms can or can in aryl, not exist), (iv) aralkyl (comprises and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, with ring-type or acyclic, and wherein heteroatoms can or can be not in the aryl of aralkyl or moieties, do not exist), or (v) alkaryl (comprises and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, and ring-type or acyclic, and wherein heteroatoms can or can be not in the aryl of alkaryl or moieties, do not exist), wherein the two or more substituting groups on phenyl or the pyrazolone ring can be combined together to form ring and n represents integer 1,2 or 3.
Scheme 2. is according to the colorant compound of the following formula of scheme 1:
Figure A20061016318100111
Scheme 3. is according to the colorant compound of the following formula of scheme 1:
Figure A20061016318100121
Scheme 4. is according to the colorant compound of scheme 1, and wherein at least one of A, E, G and J is alkyl, and condition is when A is at least one alkyl, m be at least 1 and condition be when E is at least one alkyl, p is at least 1.
Scheme 5. is according to the colorant compound of scheme 4, and wherein alkyl is a substituted alkyl.
Scheme 6. is according to the colorant compound of scheme 4, and wherein alkyl is a substituted alkyl not.
Scheme 7. wherein comprises at least one heteroatoms according to the colorant compound of scheme 4 in the alkyl.
Scheme 8. does not wherein comprise heteroatoms according to the colorant compound of scheme 4 in the alkyl.
Scheme 9. is according to the colorant compound of scheme 1, and wherein at least one of A, E, G and J is aryl, and condition is when A is at least one aryl, m be at least 1 and condition be when E is at least one aryl, p is at least 1.
Scheme 10. is according to the colorant compound of scheme 9, and wherein aryl is a substituted aryl.
Scheme 11. is according to the colorant compound of scheme 9, and wherein aryl is a unsubstituting aromatic yl.
Scheme 12. wherein comprises at least one heteroatoms according to the colorant compound of scheme 9 in the aryl.
Scheme 13. does not wherein comprise heteroatoms according to the colorant compound of scheme 9 in the aryl.
Scheme 14. is according to the colorant compound of scheme 1, wherein at least one of A, E, G and J is aralkyl or alkaryl, and condition is when A is at least one aralkyl or alkaryl, and m is at least 1, with condition be when E is at least one aralkyl or alkaryl, p is at least 1.
Scheme 15. is according to the colorant compound of scheme 14, and wherein aralkyl or alkaryl are substituted aralkyl or alkaryl.
Scheme 16. is according to the colorant compound of scheme 14, and wherein aralkyl or alkaryl are unsubstituting aromatic alkyl or alkaryl.
Scheme 17. wherein comprises at least one heteroatoms in aralkyl or the alkaryl according to the colorant compound of scheme 14.
Scheme 18. does not wherein comprise heteroatoms in aralkyl or the alkaryl according to the colorant compound of scheme 14.
Scheme 19. is according to the colorant compound of scheme 1; A wherein; at least one of E and G is to be selected from following substituting group: hydroxyl; halogen atom; amido; imido grpup; ammonium group; cyano group; the pyridine group; pyridine  group; ether group; aldehyde group; ketone groups; ester group; amide group; carbonyl; thiocarbonyl; sulfate group; sulfonate ester group; sulfonic acid group; sulfide group; sulfoxide radicals; phosphine groups; the  group; bound phosphate groups; nitrile group; sulfydryl; nitro; nitroso-group; sulfuryl group; acyl group; azo group; isocyano group; the carboxylate group; hydroxy-acid group; urethane group; urea groups; or its mixture; condition is when A is at least one substituting group; m is at least 1; with condition be when E is at least one substituting group, p is at least 1.
Scheme 20. is according to the colorant compound of scheme 1, and wherein n is 1.
Scheme 21. is according to the colorant compound of scheme 1, and wherein n is 2.
Scheme 22. is according to the colorant compound of scheme 1, and wherein n is 3.
Scheme 23. is according to the colorant compound of scheme 1, and wherein M is a lanthanide series metal.
Scheme 24. is according to the colorant compound of scheme 1, and wherein M is chromium, iron, cobalt, molybdenum, tungsten, ruthenium, osmium, rhodium, iridium, manganese, rhenium, vanadium, niobium, tantalum, titanium, zirconium, hafnium, scandium, yttrium, lanthanum, zinc, aluminium or its mixture.
Scheme 25. is according to the colorant compound of scheme 1, and wherein M is chromium, iron, cobalt or its mixture.
Scheme 26. is according to the colorant compound of scheme 1, and wherein M is a chromium.
Scheme 27. is according to the colorant compound of the following formula of scheme 1:
Figure A20061016318100141
Figure A20061016318100161
Or
Figure A20061016318100162
Scheme 28. is according to the colorant compound of the following formula of scheme 1:
Figure A20061016318100163
Scheme 29. is according to the colorant compound of scheme 1, wherein R 1, R 2And R 3Each is hydrogen atom or alkyl independently of one another, comprises linear and branching, saturated and unsaturated, ring-type and acyclic, and replacement and substituted alkyl not, and heteroatoms wherein, as oxygen, nitrogen, sulphur, silicon, phosphorus, boron etc. can or can in alkyl, not exist.
Scheme 30. is according to the colorant compound of scheme 29, and wherein at least one alkyl is linear.
Scheme 31. is according to the colorant compound of scheme 29, and wherein at least one alkyl is a branching.
Scheme 32. is according to the colorant compound of scheme 29, and wherein at least one alkyl replaces.
Scheme 33. is according to the colorant compound of scheme 29, and wherein at least one alkyl is unsubstituted.
Scheme 34. wherein contains heteroatoms at least one alkyl according to the colorant compound of scheme 29.
Scheme 35. does not wherein contain heteroatoms at least one alkyl according to the colorant compound of scheme 29.
Scheme 36. is according to the colorant compound of scheme 29, wherein R 1, R 2And R 3Mutually the same.
Scheme 37. is according to the colorant compound of scheme 29, wherein R 1, R 2And R 3At least two differ from one another.
Scheme 38. is according to the colorant compound of scheme 29, wherein R 1, R 2And R 3All three differ from one another.
Scheme 39. is according to the colorant compound of scheme 29, and wherein compound has following formula:
Or
Figure A20061016318100181
Scheme 40. is according to the colorant compound of scheme 29, and wherein compound has following formula:
Figure A20061016318100182
Or
Figure A20061016318100183
Scheme 41. is according to the colorant compound of scheme 29, and wherein compound has following formula:
Figure A20061016318100191
Or
Figure A20061016318100192
Scheme 42. is according to the colorant compound of scheme 29, and wherein compound has following formula:
Or
Scheme 43. is according to the colorant compound of scheme 29, and wherein compound has following formula:
Or
Scheme 44. is according to the colorant compound of scheme 29, and wherein compound has following formula:
Figure A20061016318100211
Or
Scheme 45. is according to the colorant compound of scheme 1, wherein R 1, R 2And R 3At least one aryl, aralkyl or alkaryl.
Scheme 46. is according to the colorant compound of scheme 45, and wherein aryl, aralkyl or alkaryl replace.
Scheme 47. is according to the colorant compound of scheme 45, and wherein aryl, aralkyl or alkaryl are unsubstituted.
Scheme 48. wherein comprises at least one heteroatoms in aryl, aralkyl or the alkaryl according to the colorant compound of scheme 45.
Scheme 49. does not wherein comprise heteroatoms in aryl, aralkyl or the alkaryl according to the colorant compound of scheme 45.
Colorant compound at this open following formula:
Figure A20061016318100221
With
Each A wherein; each E and each G represent the substituting group on phenyl or the pyrazolone ring independently of one another; (comprise linearity and branching as (but being not limited to) alkyl; saturated and unsaturated; ring-type and acyclic; and replace and substituted alkyl not; and heteroatoms wherein; as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can in alkyl, not exist); in having an embodiment of at least 1 carbon atom; with have no more than 50; in the various embodiments of 18 or 2 carbon atoms; although the number of carbon atom can be beyond these scopes; aryl (comprises and replacing and unsubstituting aromatic yl; and heteroatoms wherein; as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can in aryl, not exist); in having the various embodiments of at least 5 or 6 carbon atoms; with have no more than 20; in the various embodiments of 14 or 10 carbon atoms; although the number of carbon atom can be beyond these scopes; as phenyl; naphthyl; anthryl etc.; aralkyl (comprises and replacing and unsubstituting aromatic alkyl; wherein the moieties of aralkyl can be linearity or branching; saturated or unsaturated; with ring-type or acyclic; and heteroatoms wherein; as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can be not in the aryl of aralkyl or moieties, do not exist); in having the various embodiments of at least 6 or 7 carbon atoms; with have no more than 30; in the various embodiments of 18 or 12 carbon atoms; although the number of carbon atom can be beyond these scopes; as benzyl etc.; alkaryl (comprises and replacing and substituted alkaryl not; wherein the moieties of alkaryl can be linearity or branching; saturated or unsaturated; with ring-type or acyclic; and heteroatoms wherein; as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can be not in the aryl of alkaryl or moieties, do not exist); in having the various embodiments of at least 6 or 7 carbon atoms; with have no more than 30; 18; or in the various embodiments of 12 carbon atoms; although the number of carbon atom can be beyond these scopes; as tolyl etc.; hydroxyl; halogen atom; amido (comprises primary; the second month in a season and tertiary amine groups); imido grpup; ammonium group; cyano group; the pyridine group; pyridine  group; ether group; aldehyde group; ketone groups; ester group; amide group; carbonyl; thiocarbonyl; sulfate group; sulfonate ester group; sulfonic acid group; sulfide group; sulfoxide radicals; phosphine groups; the  group; bound phosphate groups; nitrile group; sulfydryl; nitro; nitroso-group; sulfuryl group; acyl group; azo group; isocyano group; the carboxylate group; hydroxy-acid group; urethane group; urea groups etc.; wherein G also can be a hydrogen atom; m is an integer 0; 1 or 2; p is an integer 0; 1; 2; 3 or 4 and J represent (i) hydrogen atom, (ii) alkyl (comprises linearity and branching; saturated and unsaturated; ring-type and acyclic; and replace and substituted alkyl not; and heteroatoms wherein; as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can in alkyl, not exist), in having an embodiment of at least 1 carbon atom and have no more than 50; in the various embodiments of 18 or 2 carbon atoms; although the number of carbon atom can be beyond these scopes; (iii) aryl (comprises replacing and unsubstituting aromatic yl, and heteroatoms wherein, as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can in aryl, not exist); have the various embodiments of at least 5 or 6 carbon atoms; with have no more than 20; in the various embodiments of 14 or 10 carbon atoms, although the number of carbon atom can be beyond these scopes, as phenyl; naphthyl; anthryl etc.; (iv) aralkyl (comprises and replacing and unsubstituting aromatic alkyl; wherein the moieties of aralkyl can be linearity or branching; saturated or unsaturated; with ring-type or acyclic, and heteroatoms wherein, as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can be not in the aryl of aralkyl or moieties, do not exist); in having the various embodiments of at least 6 or 7 carbon atoms; with have no more than 30; in the various embodiments of 18 or 12 carbon atoms, although the number of carbon atom can be beyond these scopes, as benzyl etc.; or (v) alkaryl (comprises and replacing and substituted alkaryl not; wherein the moieties of alkaryl can be linearity or branching; saturated or unsaturated; with ring-type or acyclic, and heteroatoms wherein, as oxygen; nitrogen; sulphur; silicon; phosphorus; boron etc. can or can be not in the aryl of alkaryl or moieties, do not exist); in having the various embodiments of at least 6 or 7 carbon atoms; with have no more than 30; in the various embodiments of 18 or 12 carbon atoms, although the number of carbon atom can be beyond these scopes, as tolyl etc.; substituted alkyl wherein; aryl; substituting group on aralkyl and the alkaryl can be (but being not limited to) hydroxyl; halogen atom; amido (comprises primary; the second month in a season or tertiary amine groups); imido grpup; ammonium group; cyano group; the pyridine group; pyridine  group; ether group; aldehyde group; ketone groups; ester group; amide group; carbonyl; thiocarbonyl; sulfate group; sulfonate ester group; sulfonic acid group; sulfide group; sulfoxide radicals; phosphine groups; the  group; bound phosphate groups; nitrile group; sulfydryl; nitro; nitroso-group; sulfuryl group; acyl group; azo group; isocyano group; the carboxylate group; hydroxy-acid group; urethane group; urea groups etc., wherein the two or more substituting groups on phenyl or the pyrazolone ring can be combined together to form ring.These tinting materials comprise the color-developing compounds derived from following formula: compound:
With
Figure A20061016318100242
The number of the electric charge in integer " n " the expression color bodies compound complex compound and the counter cation of existence.This integer is at least 1 and also can is 2 or 3.
These compound metallizing things form complex compound together to form color-developing compounds.Suitable metal M comprises any metal that forms complex compound with above-claimed cpd, and wherein complex compound has at least-1 negative charge.The example of suitable metal includes, but is not limited to chromium, iron, cobalt, molybdenum, tungsten, ruthenium, osmium, rhodium, iridium, manganese, rhenium, vanadium, niobium, tantalum, titanium, zirconium, hafnium, scandium, yttrium, lanthanum, zinc, aluminium, lanthanide series metal etc., with and composition thereof.
Although be not subject to any specific theory, believe that the complex compound of formation is as follows:
Figure A20061016318100251
Wherein dotted line and arrow are illustrated in the coordinate bond between the lone-pair electron on nitrogen-atoms and the atoms metal.Because each gives negative charge to the complex compound that obtains Sauerstoffatom, so the acquisition electric charge of compound depends on the valence state of metal.
Some object lessons that are used for the suitable color-developing compounds complex compound of compound disclosed herein include, but is not limited to following material:
Figure A20061016318100261
Figure A20061016318100281
Deng, with and composition thereof.
The color-developing compounds complex compound has at least-1 negative charge, and correspondingly associates with counter ion.Counter ion have following formula:
Figure A20061016318100291
R wherein 1, R 2And R 3Each can be (i) hydrogen atom independently of one another, (ii) alkyl (comprises linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and substituted alkyl not, and heteroatoms wherein, as oxygen, nitrogen, sulphur, silicon, phosphorus, boron etc. can or can in alkyl, not exist), in having an embodiment of at least 1 carbon atom, with have no more than 150, in the various embodiments of 54 or 48 carbon atoms, although the number of carbon atom can be beyond these scopes, (iii) aralkyl (comprises and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and heteroatoms wherein, as oxygen, nitrogen, sulphur, silicon, phosphorus, boron etc. can or can be not in the aryl of aralkyl or moieties, do not exist), in having the various embodiments of at least 6 or 7 carbon atoms, with have no more than 56, in the various embodiments of 24 or 18 carbon atoms, although the number of carbon atom can be beyond these scopes, as benzyl etc., or (iv) alkaryl (comprises and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and heteroatoms wherein, as oxygen, nitrogen, sulphur, silicon, phosphorus, boron etc. can or can be not in the aryl of alkaryl or moieties, do not exist), in having the various embodiments of at least 6 or 7 carbon atoms, with have no more than 56, in the various embodiments of 24 or 18 carbon atoms, although the number of carbon atom can be beyond these scopes, as tolyl etc., condition is R 1+ R 2+ R 3The overall number of middle carbon atom and heteroatoms (getting rid of the atom in any substituting group) is at least 18,19,20,21,22,23 or 24 in various embodiments, wherein R 1+ R 2+ R 3In the overall number of carbon atom and heteroatoms (getting rid of the atom in any substituting group) in various embodiments no more than 150; 54 or 48; although the overall number of carbon atom can be beyond this scope; substituted alkyl wherein; aryl; substituting group on aralkyl and the alkaryl can be (but being not limited to) hydroxyl; halogen atom; amido; imido grpup; ammonium group; cyano group; the pyridine group; pyridine  group; ether group; aldehyde group; ketone groups; ester group; amide group; carbonyl; thiocarbonyl; sulfate group; sulfonate ester group; sulfonic acid group; sulfide group; sulfoxide radicals; phosphine groups; the  group; bound phosphate groups; nitrile group; sulfydryl; nitro; nitroso-group; sulfuryl group; acyl group; azo group; isocyano group; the carboxylate group; hydroxy-acid group; urethane group; urea groups; its mixtures etc., wherein two or more substituting groups can be combined together to form ring.In one embodiment, R 1, R 2And R 3Mutually the same.In another embodiment, R 1, R 2And R 3At least two differ from one another.In another embodiment, R 1, R 2And R 3All three differ from one another.
Colorant compound disclosed herein can be by any required or effective means preparation.For example, have different counter ion or adopt the color-developing compounds of free acid form commercially to obtain and counter ion can be substituted by required counter ion.The metallized azo dyestuff can be by any required or effective means, as at for example " British Intelligence ObjectivesSubcommittee Report 961, " Publications Board No.86139, Library ofCongress, Washington, D.C.1947, pp.71-72,110,149-151, the method of describing in 160,163,164 is carried out.Required counter ion also can be usually derived from commercially available amine compound.The primary, the second month in a season and tertiary amine also can prepare, as in for example Comprehensive OrganicTransformations-A Guide to Functional Group Preparations, 2 NdEd., Richard C.Larock, Wiley-VCH, 1999 ISBN 0-471-19031-4 NewYork are described in the NY.
For example, in one embodiment, color-developing compounds and counter ion can heat up to ion-exchange complete together derived from its amine compound, subsequently distilling off solvent (if using solvent) and reclaim the colorant compound of preparation like this.
Can adopt the color-developing compounds of any required or effective relative populations and counter ion amine compound derived from it.When the electric charge on the color-developing compounds is-1, relative populations can be at least 0.1,0.5 or 0.9 mole of each mole of color-developing compounds amine compound for example in various embodiments, with no more than 3,2 or 1.1 moles of each mole of color-developing compounds amine compound in various embodiments, although relative populations can be beyond these scopes.When the electric charge on the color-developing compounds was-2, the quantity of amine compound doubled certainly, and when the electric charge on the color-developing compounds was higher, therefore the quantity of amine compound can regulate certainly.
When using solvent, can adopt any required or active solvent.The example of suitable solvent comprises alcohol such as methyl iso-butyl ketone (MIBK), methylethylketone, acetone, methyl alcohol, ethanol, n-propyl alcohol, Virahol, fourth, with and composition thereof.
Reactant adopts any required or effective quantity to exist in solvent, in various embodiments, be at least every liter of solvent of 1,225 or 450 gram reactants, with in various embodiments no more than 2,000,1, every liter of solvent of 000 or 500 gram reactants exists, although the relative populations of reactant and solvent can be beyond these scopes.
Reactant can be heated to any required or significant temp, in various embodiments at least 25 ℃, 65 ℃ or 110 ℃ with in various embodiments, be not higher than 150 ℃, 125 ℃ or 110 ℃, although temperature can be beyond these scopes.
Reactant can heat any required or effective time, in various embodiments at least 1,12 or 16 hour and in various embodiments no more than 7,1 or 0.75 days, although the time can be beyond these scopes.
Thereafter, Zhi Bei colorant compound can be by any required or effective ways like this, and as gone into solvent etc. by distillation, vacuum, quenching and reclaim, wherein product is insoluble in the described solvent (as water).
Example I
The 2-that magnet, silicone oil bath, the magnetic that applies to assembling TEFLON  stirs hot plate and condenser rises in the 3-neck round-bottomed flask and adds 1,100g methyl iso-butyl ketone (MIBK) (from Aldrich ChemicalCo., Milwaukee, WI acquisition).Begin to stir and the solvent black 45 free acid dyestuffs of following formula (250g, 0.275 mole, from Orient Chemical Industries Ltd, Osaka, Japan obtains) are joined in the flask.
Figure A20061016318100311
Oil bath is heated to 120 ℃ dissolved up to dyestuff in 2 hours fully.(ARMEEN  2HT, from Akzo Nobel, McCook, Illinois obtains) adds subsequently with 196.3g (0.20 mole) distearyl amine, and subsequently with reaction mixture refluxed 16 hours.Connect water distilling apparatus subsequently and by means of the nitrogen inlet distilling off solvent.When distillation seems complete, system is applied vacuum.Increase vacuum gradually to prevent foaming and to keep 16 hours down at 120 ℃.Then flask is transferred to 120 ℃ baking oven and put upside down fixingly, and collect product.Believe that product has following formula:
Example II
In the 100-milliliter 3-neck round-bottomed flask of magnet, silicone oil bath, magnetic stirring hot plate and condenser that assembling TEFLON  applies, add 75g methyl iso-butyl ketone (MIBK) (from AldrichChemical Co., Milwaukee, WI acquisition).Begin to stir and solvent black 45 free acid dyestuffs (10g, 0.015 mole, from Orient Chemical Industries Ltd, Osaka, Japan obtains) are joined in the flask.Oil bath is heated to 120 ℃ dissolved up to dyestuff in 0.5 hour fully.The PA28 of 6.2g (0.015 mole) (from Tomah Products Inc., Milton, Wisconsin obtains) is added subsequently, and subsequently with reaction mixture refluxed 16 hours.Connect water distilling apparatus subsequently and by means of the nitrogen inlet distilling off solvent.When distillation seems complete, then flask is transferred to 120 ℃ baking oven and fixed 1 hour, and collect product with putting upside down.Believe that product has following formula:
EXAMPLE III
Repeat the process of example II, difference is that the SA19.3 (from Tomah Products Inc., Milton, Wisconsin acquisition) of 5.11g (0.015 mole) substitutes the PA28 of 6.2g (0.015 mole).Believe that product has following formula:
Figure A20061016318100331
EXAMPLE IV
In the 100-milliliter 3-neck round-bottomed flask of magnet, silicone oil bath, magnetic stirring hot plate and condenser that assembling TEFLON  applies, add 35g methyl iso-butyl ketone (MIBK) (from AldrichChemical Co., Milwaukee, WI acquisition).Begin to stir and solvent black 45 free acid dyestuffs (5g, 0.0075 mole, from Orient Chemical Industries Ltd, Osaka, Japan obtains) are joined in the flask.Oil bath is heated to 120 ℃ dissolved up to dyestuff in 0.5 hour fully.2.9g (0.0075 mole) PROPOMEEN O/12 (from AkzoNobel, McCook, Illinois obtains) is added subsequently, and subsequently with reaction mixture refluxed 16 hours.Connect water distilling apparatus subsequently and by means of the nitrogen inlet distilling off solvent.When distillation seems complete, then flask is transferred to 120 ℃ baking oven and put upside down and fix 1 hour, collect product.Believe that product has following formula:
Figure A20061016318100332
EXAMPLE V
Repeat the process of example II, difference is 10.3g (0.015 mole) three-hexadecylamine (ARMEEN  316, from Akzo Nobel, McCook, Illinois obtains) is substituted the PA28 of 6.2g (0.015 mole).Believe that product has following formula:
Figure A20061016318100341
Example VI
Repeat the process of example II, difference is 7.8g (0.015 mole) three-lauryl amine (ARMEEN  312, from Akzo Nobel, McCook, Illinois obtains) is substituted the PA28 of 6.2g (0.015 mole).Believe that product has following formula:
Figure A20061016318100342
Example VII A
Use CI 12695 to replace solvent black 45 (CI 12195) to repeat the process of example I-VI as the free acid dyestuff.Believe and obtain similar result.
Example VII A I
Use CI 12696 to replace solvent black 45 (CI 12195) to repeat the process of example I-VI as the free acid dyestuff.Believe and obtain similar result.
Example I X
Use CI 12716 to replace solvent black 45 (CI 12195) to repeat the process of example I-VI as the free acid dyestuff.Believe and obtain similar result.
Embodiment X
Use CI 11836 to replace solvent black 45 (CI 12195) to repeat the process of example I-VI as the free acid dyestuff.Believe and obtain similar result.
Embodiment XI
Use CI 12196 to replace solvent black 45 (CI 12195) to repeat the process of example I-VI as the free acid dyestuff.Believe and obtain similar result.
Embodiment XII
Use CI 12205 to replace solvent black 45 (CI 12195) to repeat the process of example I-VI as the free acid dyestuff.Believe and obtain similar result.
Printing ink embodiment
Ink composite is prepared by following method.All ink compositions except that tinting material are joined in the stainless steel beaker.Then with the mixture fusion together in baking oven that obtains, subsequently by in the cover of controlled temperature, under the temperature identical, stirring 0.3 hour and blend with baking oven, for printing ink A and B and comparative ink 1 110 ℃ temperature with for the temperature of printing ink C at 135 ℃.In this mixture, add tinting material then.After stirring other 2 hours, use Whatman#3 filter paper under the pressure of 15 pound per square inches, to filter by the MOTT  equipment (obtaining) that is heated in the printing ink that forms like this from MottMetallurgical.The filtering phase change ink impouring mould and the permission that form are like this solidified to form ink strip.Printing ink prepares from following composition: and polyethylene wax (PE 500, from Baker Petrolite, and Tulsa, OK obtains); Polyethylene wax (PE 655, from Baker Petrolite, and Tulsa, OK obtains); The branching triamide of following formula:
Figure A20061016318100351
Wherein each mean value of p, q and r is 35, as at United States Patent (USP) 6,860, prepares described in 930 the example II; (obtain from the reaction of following material: monovalent is from Uniqema for four acid amides, New Castle, C-36 dimer acids that DE obtains and two equivalent quadrols and UNICID  700 are (from Baker Petrolite, Tulsa, OK obtains, and contains the long chain hydrocarbon of terminal carboxylic acid group), as at United States Patent (USP) 6, preparation described in 174,937 the embodiment 1); The stearyl stearamide wax (KEMAMIDE  S-180, from CromptonCorporation, Greenwich, CT obtains); (triglyceride level of staybelite (rosin) acid is available from Arakawa Chemical Industries, Ltd.) for the KE-100 resin; From two equivalent ABITOL  E hydrogen rosinyl alcohol (from Hercules Inc., Wilmington, DE obtains) and the urethane resin of the reaction acquisition of monovalent isophorone diisocyanate, as at United States Patent (USP) 5, preparation (hereinafter referred to as urethane resin #1) described in 782,966 the embodiment 1; Urethane resin, it is the adducts of three equivalent isocyanic acid stearyl and glycerols alcohol, as at United States Patent (USP) 6,309, prepares described in 453 the embodiment 4 (hereinafter referred to as urethane resin #2); NAUGUARD  445 oxidation inhibitor (from Uniroyal Chemical Co., Middlebury, CT obtains); DISPERSE ORANGE 30 200 47 dyestuffs (DO-47, from Keystone AnilineCorporation, Chicago, IL obtains) and as at the tinting material for preparing described in the example I.In being listed in the table below for the quantity of every kind of composition of every kind of printing ink:
Printing ink A B C 1
Polyethylene wax 500 55.45 52.28 0 56.50
Polyethylene wax 655 0 0 35.95 0
The branching triamide 10.99 12.29 0 11.2
Four acid amides 0 0 13.41 0
The stearyl stearamide wax 13.53 15.03 23.99 13.60
The KE-100 resin 9.70 10.86 0 10.20
Urethane resin #1 0 0 12.26 0
Urethane resin #2 3.96 4.37 8.02 4.0
Oxidation inhibitor 0.18 0.17 0.20 0.20
DO-47 0.20 0.20 0.20 0.20
The example I tinting material 5.99 4.80 5.99 0
Solvent black 45 0 0 0 4.10
For estimating the colorant dissolubility in the printing ink base-material, the spectral intensity of printing ink measuring under 580nm as colorant dissolubility in filtration and the unfiltered printing ink.Filter out any undissolved dyestuff in the printing ink, cause and do not filter printing ink and compare the littler spectral intensity of filtering printing ink.Therefore, the spectral intensity of filtration printing ink is measuring of colorant dissolubility with the ratio that does not filter the spectral intensity of printing ink (" SS ratio "); Than the degree that significantly is lower than 1, its indicates the poor solubleness of dyestuff in printing ink base-material to SS.Second-order transition temperature (T g) use Rheometrics Solid Analyzer (RSA II) to measure by dynamic mechanical analysis.Fusing point and zero pour use DUPONT 2100 calorimeters to measure by dsc (DSC).
Printing ink A B C 1
Not filter light spectral intensity under the 380nm 1014 812 1030 884
Not filter light spectral intensity under the 480nm 973 827 959 808
Not filter light spectral intensity under the 580nm 1142 886 1115 928
Filter light spectral intensity under the 380nm 993 796 1028 543
Filter light spectral intensity under the 480nm 841 724 957 490
Filter light spectral intensity under the 580nm 1129 883 1111 545
SS is than (580nm filters down/do not filter) 0.99 1.00 1.00 0.69
Viscosity under 110 ℃ (centipoise) (filtering) 10.45 10.83 --- 9.59
Viscosity under 140 ℃ (centipoise) (filtering) --- --- 10.86 ---
T g 9.63 11.8 --- ---
Fusing point (℃) 80.2 80.2 --- ---
Zero pour (℃) 67.2，72.4 68.7，74.5 --- ---
Printing ink A and B are incorporated into improvement to print among the XEROX  PHASER  8400 that prints down at 110 ℃ and successfully.Be incorporated into printing ink C among the XEROX  PHASER  8400 that prints under the standard printing temperature and successfully printing.Shown in data, the tinting material for preparing in example I dissolves in printing ink better.On the contrary, commercial tinting material dissolving is relatively poor, shown in being compared with the spectral intensity of not filtering printing ink by the filtration that is 0.69 under 580 nanometers.

Claims (7)

1. the colorant compound of following formula:
Figure A2006101631810002C1
R wherein 1, R 2And R 3Each is hydrogen atom independently of one another, alkyl, comprise linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and substituted alkyl not, and wherein heteroatoms can or can in alkyl, not exist, aralkyl, comprise and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and wherein heteroatoms can or can be not in the aryl of aralkyl or moieties, do not exist, or alkaryl, comprise and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, ring-type or acyclic, and replacement or unsubstituted, and wherein heteroatoms can or can be not in the aryl of alkaryl or moieties, do not exist, condition is R 1+ R 2+ R 3The middle atom of getting rid of in any substituting group, carbon atom and heteroatomic overall number are at least about 18, M is an atoms metal, each A, each E and each G represent the substituting group on phenyl or the pyrazolone ring independently of one another, wherein G also can be a hydrogen atom, m is an integer 0,1 or 2, p is an integer 0,1,2,3 or 4, J represents (i) hydrogen atom, (ii) alkyl, comprise linearity and branching, saturated and unsaturated, ring-type and acyclic, and replace and substituted alkyl not, and wherein heteroatoms can or can in alkyl, not exist, (iii) aryl, comprise and replacing and unsubstituting aromatic yl, and wherein heteroatoms can or can in aryl, not exist, (iv) aralkyl, comprise and replacing and unsubstituting aromatic alkyl, wherein the moieties of aralkyl can be linearity or branching, saturated or unsaturated, with ring-type or acyclic, and wherein heteroatoms can or can be not in the aryl of aralkyl or moieties, do not exist, or (v) alkaryl, comprise and replacing and substituted alkaryl not, wherein the moieties of alkaryl can be linearity or branching, saturated or unsaturated, with ring-type or acyclic, and wherein heteroatoms can or can be not in the aryl of alkaryl or moieties, do not exist, wherein the two or more substituting groups on phenyl or the pyrazolone ring can be combined together to form ring and n represents integer 1,2 or 3.
2. according to the colorant compound of the following formula of claim 1:
3. according to the colorant compound of the following formula of claim 1:
4. according to the colorant compound of the following formula of claim 1:
Figure A2006101631810004C1
Figure A2006101631810005C1
5. according to the colorant compound of the following formula of claim 1:
Figure A2006101631810006C2
6. according to the colorant compound of claim 1, R wherein 1, R 2And R 3Each is hydrogen atom or alkyl independently of one another, comprises linear and branching, saturated and unsaturated, ring-type and acyclic, and replacement and substituted alkyl not, and heteroatoms wherein, as oxygen, nitrogen, sulphur, silicon, phosphorus, boron etc. can or can in alkyl, not exist.
7. according to the colorant compound of claim 6, wherein compound has following formula:
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CN102161641A (en) * 2009-12-25 2011-08-24 住友化学株式会社 Pyridone complex
CN102796400A (en) * 2011-05-25 2012-11-28 上海雅运纺织化工股份有限公司 Yellow azo metallized dye composition, method and application thereof
CN102796400B (en) * 2011-05-25 2013-12-04 上海雅运纺织化工股份有限公司 Yellow azo metallized dye composition, method and application thereof
CN104610777A (en) * 2015-01-13 2015-05-13 青岛双桃精细化工（集团）有限公司 Red complex dye used for wool/chinlon blend dyeing
CN104610777B (en) * 2015-01-13 2017-07-04 青岛双桃精细化工（集团）有限公司 A kind of red composite dye for hair brocade blend dyeing

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CN1974674B (en) 2014-04-02
EP1808463B1 (en) 2010-10-06
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BRPI0604984B1 (en) 2018-02-14
KR20070057047A (en) 2007-06-04
CA2568927C (en) 2011-01-25
JP5117707B2 (en) 2013-01-16
EP1808463A2 (en) 2007-07-18
CA2568927A1 (en) 2007-05-30
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US20070123701A1 (en) 2007-05-31

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